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Quaternary pyridinium salts from olefins, pyridine and chlorine or bromine
Author(s) -
Wheeler D. H.,
Gross J.
Publication year - 1965
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02632447
Subject(s) - pyridine , chemistry , pyridinium , halogen , medicinal chemistry , organic chemistry , chlorine , carbonium ion , photochemistry , alkyl , ion
The reaction of olefins with a halogen and pyridine (or pyridine derivative) to form ॅ‐haloalkypyridinium quaternary halides has been previously reported only for the halogens bromine and iodine monochloride. In the present study, this reaction has been extended to the use of chlorine as halogen, and to the internal double bonds of unsaturated acids and derivatives. Oleic acid, methyl oleate, methyl linoleate, oleic amide and octadecene were used as olefins. Pyridine, quinoline and े‐picoline were used as the amines. Formation of the quaternaries was shown by chemical and infrared analyses. The reaction occurred rapidly at 蜢20C in excess pyridine as solvent and reagent. The probable mechanism is addition of X + to the double bond to give an ॅ‐halo‐cation plus halogen anion, followed by attack of the cation by the pyridine to form the quateruary pyridinium cation. The competing reaction of the ॅ‐balo‐cation with the halo‐anion to give the dihalide of the olefin is repressed by the large excess of pyridine used. The quaternary is not formed by reaction of the dihalide with pyridine, since methyl dichlorostearate did not react readily with pyridine. The fatty pyridinium quaternaries show biocidal activity against E. coli and M. pyogenes .